HCID 178418573, compound → HCID 178441842, compound

HRID 486494Notes

Reaction equation

HRID 486494 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][CH2:15][CH2:16][CH3:17])=[N:8][C:7]2=[O:18])(=[O:3])[CH3:2].[CH3:19][Mg]Br>O1CCCC1.C(OCC)C>[CH2:14]([C:9]1[NH:10][C:11]2[C:6]([C:7](=[O:18])[N:8]=1)=[CH:5][C:4]([C:1]([OH:3])([CH3:19])[CH3:2])=[CH:13][CH:12]=2)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178441846HCID 178441846, compound

Product 1

HCID 178441842HCID 178441842, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.00 g of 6-acetyl-2-butyl-4-(1H)-quinazolinone in 250 ml of dry tetrahydrofuran, cooled to 0° C., is added dropwise 16.4 ml of 3.0M methylmagnesium bromide in diethyl ether. The reaction is stirred at 0° C. for 0.5 hours and then allowed to warm to room temperature followed by quenching with 100 ml of saturated ammonium chloride solution. The mixture is diluted with 50 ml of water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 100:0.25 chloroform-reethanol to give 2.75 g of the desired product as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. customby quenching with 100 ml of saturated ammonium chloride solution
  3. additionThe mixture is diluted with 50 ml of water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash chromatography on silica gel
  10. washeluting with 100:0.25 chloroform-reethanol

Sources & evidence

ORD record
ord-2f025cd97ac3423b8b0fa7c0b0cf05a9
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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